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N(2)-L-alanyl-L-glutamine synthesis method

A technology of glutamine and synthetic methods, applied in the direction of peptides, etc., can solve the problems of cumbersome operation steps, little application prospect, and high price, and achieve the effect of reducing cost, low cost, and low price

Inactive Publication Date: 2013-08-28
BAODING LONGRUI PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Using this idea to synthesize N(2)-L-alanyl-L-glutamine, the operation steps are relatively cumbersome, and the relatively expensive N-hydroxysuccinimide and DCC will be used at the same time, so this method is used at home and abroad. There are not many manufacturers who synthesize N(2)-L-alanyl-L-glutamine
In addition, some literatures have reported the synthesis of N(2)-L-alanyl-L-glutamine, but the operation steps are cumbersome and only suitable for laboratory synthesis, and the application prospect of industrialization is not great

Method used

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Experimental program
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Effect test

Embodiment 1

[0036] 1. Synthesis of pyruvyl-L-glutamine

[0037]Add 73g (0.5mol) L-glutamine to 500mL water, add 10% NaOH dropwise at 0°C to adjust the pH to 10, keep the temperature, add 68.9g (0.65mol) pyruvate chloride dropwise, and keep the pH during the dropwise addition Value is about 10. After the dropwise addition, react at 0-5°C for 30 minutes, rise to room temperature and continue the reaction for 4 hours, then stop the reaction. Under ice-bath conditions, add 2mol / L HCl dropwise to adjust the pH to 1-2, and stand overnight at 0-5°C, a large amount of white solids precipitate, filter, wash with a small amount of ice water, and dry in vacuo to obtain 77.8g of white crystals, with a yield of 74 %, m.p.83-85°C. 1 H-NMR (CDCl 3 ), δ: 8.03(s, 1H), 7.16(s, 2H), 4.56(t, 1H), 2.17(s, 3H), 2.12(m, 2H), 2.05(t, 2H). EI-MS m / z: 216.

[0038] 2. Synthesis of N(2)-2'-hydroxyimino-propionyl-L-glutamine and

[0039] Dissolve 54g (0.25mol) of pyruvic glutamine in 150mL of ethanol, add drop...

Embodiment 2

[0043] 1. Synthesis of pyruvyl-L-glutamine

[0044] Add 73g (0.5mol) L-glutamine to 600mL water, add 5% KOH dropwise at 2°C to adjust the pH to 11, keep the temperature, add 0.8mol pyruvate chloride dropwise, and keep the pH at about 11 during the dropwise addition . After the dropwise addition, react at 0-3°C for 40 minutes, rise to room temperature and continue the reaction for 5 hours, then stop the reaction. Under the condition of ice bath, add 1mol / LH dropwise 2 SO 4 Adjust the pH to 2-3, and let it stand overnight at 0-3°C. A large amount of white solids precipitated out. Filter, wash with a small amount of ice water, and dry in vacuo to obtain 77.8 g of white crystals, yield 76%, m.p.83-85°C. 1 H-NMR (CDCl 3 ), δ: 8.03(s, 1H), 7.16(s, 2H), 4.56(t, 1H), 2.17(s, 3H), 2.12(m, 2H), 2.05(t, 2H). EI-MS m / z: 216.

[0045] 2. Synthesis of N(2)-2'-benzyloxyimino-propionyl-L-glutamine

[0046] Dissolve 54g (0.25mol) of pyruvylglutamine in 150mL of methanol, add 36.9g (0.3m...

Embodiment 3

[0050] 1. Synthesis of pyruvyl-L-glutamine

[0051] Add 73g (0.5mol) of L-glutamine to 400mL of water, add 8% NaOH dropwise at 1°C to adjust the pH to 9, keep the temperature, add 1mol of pyruvate chloride dropwise, and keep the pH at about 9 during the dropwise addition. After the dropwise addition, react at 5-10°C for 50 minutes, rise to room temperature and continue the reaction for 6 hours, then stop the reaction. Under ice-bath conditions, add 3mol / L HCl dropwise to adjust the pH to 2-3, and stand overnight at 5-10°C, a large amount of white solids precipitated, filtered, washed with a small amount of ice water, and dried in vacuo to obtain 77.8g of white crystals with a yield of 72 %, m.p.83-85°C. 1 H-NMR (CDCl 3 ), δ: 8.03(s, 1H), 7.16(s, 2H), 4.56(t, 1H), 2.17(s, 3H), 2.12(m, 2H), 2.05(t, 2H). EI-MS m / z: 216.

[0052] 2. Synthesis of N(2)-2'-allyloxyimino-propionyl-L-glutamine

[0053] 54g (0.25mol) of pyruvyl glutamine was dissolved in 200mL of isopropanol, and 1...

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Abstract

The invention relates to an N(2)-L-alanyl-L-glutamine synthesis method. The method comprises the following steps: reacting an initial raw material L-glutamine with pyruvoyl chloride to obtain alanyl-L-glutamine, reacting alanyl-L-glutamine with hydroxylamine hydrochloride or O-alkylhydroxylamine to obtain N(2)-2'-hydroximino-propionyl-glutamine or N(2)-2'-alkoxyimino-propionyl-glutamine, and hydrogenating to obtain N(2)-L-alanyl-L-glutamine. The method has the advantages of simple operation, mild reaction conditions, stable raw material sources, low cost, safe operation, environmental protection, and wide industrialized application prospect when the method is used for synthesizing N(2)-L-alanyl-L-glutamine.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing compound N(2)-L-alanyl-L-glutamine. Background technique [0002] L-glutamine is the most abundant free amino acid in human muscle, accounting for about 60% of free amino acids in blood. L-glutamine has a very important physiological effect on the human body. It is the energy source of rapidly dividing cells such as intestinal cells, lymphocytes, and macrophages. The concentration of extracellular L-glutamine can affect the differentiation of lymphocytes and the expression of cytokines. Production, phagocytic and secretory activity of macrophages and bactericidal effect of neutrophils. Under normal circumstances, L-glutamine can be synthesized in large quantities from glutamic acid, valine, and isoleucine in muscle and other tissues, so it is regarded as a non-essential amino acid; when the human body is in a state of stress, such as trauma, surgery, b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/062
Inventor 张月忠赵俊女张志媛
Owner BAODING LONGRUI PHARMA TECH
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